Antifungal activity of pyranone and furanone derivatives, isolated from Aspergillus sp. IFM51759, against Aspergillus fumigatus

Komai, Shin-ichirou; Hosoe, Tomoo; Nozawa, Koohei; Okada, Kaoru; Takaki, Galba Maria de Campos; Fukushima, Kazutaka; Miyaji, Makato; Horie, Yoshikazu; Kawai, Ken‐ichi

doi:10.2520/myco.53.11

Cited by 20 publications

(19 citation statements)

References 6 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Based on the detailed 1 H, 13 C NMR and 2D NMR, COSY and HMBC spectra, compound (6) was identified as (Argoudelis and Zieserl, 1966;Yang et al, 1997;Komai et al, 2003), and compound (7) as (+)-(6R, 7S)-dia-asperlin, which was originally reported from Aspergillus caespitosus (Mizuba et al, 1975;Yang et al, 1997). This structure was confirmed by a synthetic method (Murayama et al, 1987).…”

Section: Extraction Purification and Identification Of Phytotoxinsmentioning

confidence: 76%

Phytotoxic metabolites from Neofusicoccum parvum, a pathogen of Botryosphaeria dieback of grapevine

et al. 2015

View full text Add to dashboard Cite

Liquid chromatography-diode array screening of the organic extract of the cultures of 13 isolates of the fungus Neofusicoccum parvum, the main causal agent of botryosphaeria dieback of grapevine, showed similar metabolites. One strain was selected for further chemical studies and led to the isolation and characterisation of 13 metabolites. Structures were elucidated through spectroscopic analyses, including one-and two-dimensional NMR and mass spectrometry, and through comparison to literature data. The isolated compounds belong to four different chemical families: five metabolites, namely, (À)-terremutin (1), (+)-terremutin hydrate (2), (+)-epi-sphaeropsidone (3) (À)-4-chloro-terremutin hydrate (4) and(+)-4-hydroxysuccinate-terremutin hydrate (5), belong to the family of dihydrotoluquinones; two metabolites, namely, (6S,7R) asperlin (6) (11), belong to the family of dihydroisocoumarins; and two of the metabolites, namely, 6-methyl-salicylic acid (12) and 2-hydroxypropyl salicylic acid (13), belong to the family of hydroxybenzoic acids. We determined the phytotoxic activity of the isolated metabolites through a leaf disc assay and the expression of defence-related genes in Vitis vinifera cells cv. Chardonnay cultured with (À)-terremutin (1), the most abundant metabolite. Finally, analysis of the brown stripes of grapevine wood from plants showing botryosphaeria dieback symptoms revealed the presence of two of the isolated phytotoxins. and (6R,7S)-dia-asperlin (7), belong to the family of epoxylactones; four metabolites, namely, (R)-(À)-mellein (8), (3R,4R)-4-hydroxymellein (9), (3R,4S)-4-hydroxymellein (10) (R)(À)-3-hydroxymellein

show abstract

Section: Extraction Purification and Identification Of Phytotoxinsmentioning

confidence: 76%

Phytotoxic metabolites from Neofusicoccum parvum, a pathogen of Botryosphaeria dieback of grapevine

et al. 2015

View full text Add to dashboard Cite

show abstract

“…Since eushearilide (1) was insoluble in water, the antimicrobial activity was determined by the paper disc method, as described in the previous paper [2,3]. The results are summarized in Table 1.…”

Section: Antimicrobial Propertymentioning

confidence: 99%

A New Antifungal Macrolide, Eushearilide, Isolated from Eupenicillium shearii

et al. 2006

Self Cite

View full text Add to dashboard Cite

In screening for antifungal substances, a new macrolide, eushearilide (1), was isolated from Eupenicillium shearii IFM54447. The structure of 1 was established to be 24-membered macrolide having a non-conjugated diene and a choline phosphate ester moetiy on the basis of detailed investigation of NMR, UV, IR and MS spectral data. Compound 1 showed antifungal activity against various fungi and yeasts, including human pathogens Aspergillus fumigatus, Trichophyton spp. and Candida spp.

show abstract

“…It has been isolated previously from several species of the fungal genera Nigrospora (Fukushima et al 1998;Trisuwan et al 2009;Wu et al2009), Xylaria (Jimenéz-Romero et al 2008, Aspergillus (Komai et al 2003), Verticillium (Khambay et al 2000), Drechslera (Krivobok et al 1994), Hirsutella (entomopathogenic) ( K r a s n o f f a n d G u p t a 1 9 9 4 ) , P a e c i l o m y c e s (entomopathogenic) (Wu et al 2012), and Phoma (Yamamoto et al 1970). Phomolactone has antifungal activity against Aspergillus fumigatus (Komai et al 2003), nematocidal activity (Khambay et al 2000), immunomodulating activity (Krivobok et al 1994), insecticide activity (Krasnoff and Gupta 1994), phytotoxic activity (Fukushima et al 1998), and weak activity against Plasmodium falciparum (Jimenéz-Romero et al 2008). Its ecological role(s) in each of these species has not been rigorously studied, but its phytotoxic, fungitoxic, and insecticidal activities may be important to the various fungi that produce phomalactone.…”

Section: Resultsmentioning

confidence: 99%

Phomalactone from a Phytopathogenic Fungus Infecting ZINNIA elegans (ASTERACEAE) Leaves

et al. 2015

View full text Add to dashboard Cite

Zinnia elegans Jacq. plants are infected by a fungus that causes dark red spots with necrosis on leaves, particularly in late spring to the middle of summer in the Mid-South of the United States. This fungal disease causes the leaves to wilt and eventually kills the plant. The fungus was isolated, cultured in potato dextrose broth, and identified as Nigrospora sphaerica by molecular techniques. Two major lactone metabolites (phomalactone and catenioblin A) were isolated from liquid culture of N. sphaerica isolated from Z. elegans. When injected into leaves of Z. elegans, phomalactone caused lesions similar to those of the fungus. The lesion sizes were proportional to the concentration of the phomalactone. Phomalactone, but not catenioblin A, was phytotoxic to Z. elegans and other plant species by inhibition of seedling growth and by causing electrolyte leakage from photosynthetic tissues of both Z. elegans leaves and cucumber cotyledons. This latter effect may be related to the wilting caused by the fungus in mature Z. elegans plants. Phomalactone was moderately fungicidal to Coletotrichum fragariae and two Phomopsis species, indicating that the compound may keep certain other fungi from encroaching into plant tissue that N. sphaerica has infected. Production of large amounts of phomalactone by N. sphaerica contributes to the pathogenic behavior of this fungus, and may have other ecological functions in the interaction of N. sphaerica with other fungi. This is the first report of isolation of catenioblin A from a plant pathogenic fungus. The function of catenioblin A is unclear, as it was neither significantly phyto- nor fungitoxic.

show abstract

Antifungal activity of pyranone and furanone derivatives, isolated from Aspergillus sp. IFM51759, against Aspergillus fumigatus

Cited by 20 publications

References 6 publications

Phytotoxic metabolites from Neofusicoccum parvum, a pathogen of Botryosphaeria dieback of grapevine

Phytotoxic metabolites from Neofusicoccum parvum, a pathogen of Botryosphaeria dieback of grapevine

A New Antifungal Macrolide, Eushearilide, Isolated from Eupenicillium shearii

Phomalactone from a Phytopathogenic Fungus Infecting ZINNIA elegans (ASTERACEAE) Leaves

Contact Info

Product

Resources

About